DE1241834B - Verfahren zur Herstellung von 5-Nitrothiophenderivaten - Google Patents
Verfahren zur Herstellung von 5-NitrothiophenderivatenInfo
- Publication number
- DE1241834B DE1241834B DE1962B0069848 DEB0069848A DE1241834B DE 1241834 B DE1241834 B DE 1241834B DE 1962B0069848 DE1962B0069848 DE 1962B0069848 DE B0069848 A DEB0069848 A DE B0069848A DE 1241834 B DE1241834 B DE 1241834B
- Authority
- DE
- Germany
- Prior art keywords
- nitrothiophene
- pyridyl
- aldehyde
- acetic anhydride
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical class [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- CHTSWZNXEKOLPM-UHFFFAOYSA-N 5-nitrothiophene-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)S1 CHTSWZNXEKOLPM-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- -1 N-acetyl compound Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JXUMCVDPMJWGSI-UHFFFAOYSA-N 5-Nitro-2-furfuryl methyl ether Chemical compound COCC1=CC=C([N+]([O-])=O)O1 JXUMCVDPMJWGSI-UHFFFAOYSA-N 0.000 description 1
- KAZMCIGKULUUMR-UHFFFAOYSA-N 6-methylpyridazin-3-amine Chemical compound CC1=CC=C(N)N=N1 KAZMCIGKULUUMR-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- QOERYXGIRHBDNW-UHFFFAOYSA-N acetic acid;5-nitrothiophene-2-carbaldehyde Chemical compound CC(O)=O.CC(O)=O.[O-][N+](=O)C1=CC=C(C=O)S1 QOERYXGIRHBDNW-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- IAIWVQXQOWNYOU-UHFFFAOYSA-N nitrofurazone Chemical compound NC(=O)NN=CC1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-UHFFFAOYSA-N 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL301268D NL301268A (enrdf_load_stackoverflow) | 1962-12-04 | ||
| BE640741D BE640741A (enrdf_load_stackoverflow) | 1962-12-04 | ||
| DE1962B0069848 DE1241834B (de) | 1962-12-04 | 1962-12-04 | Verfahren zur Herstellung von 5-Nitrothiophenderivaten |
| CH1471463A CH445519A (de) | 1962-12-04 | 1963-12-02 | Verfahren zur Herstellung neuer 5-Nitrothiophen-Derivate |
| AT966563A AT241451B (de) | 1962-12-04 | 1963-12-03 | Verfahren zur Herstellung von neuen 5-Nitrothiophen-Derivaten |
| GB4766363A GB989604A (en) | 1962-12-04 | 1963-12-03 | New 5-nitrothiophene derivatives |
| FR956024A FR1377687A (fr) | 1962-12-04 | 1963-12-04 | Procédé pour la préparation de nouveaux dérivés du 5-nitrothiophène |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1962B0069848 DE1241834B (de) | 1962-12-04 | 1962-12-04 | Verfahren zur Herstellung von 5-Nitrothiophenderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1241834B true DE1241834B (de) | 1967-06-08 |
Family
ID=6976440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962B0069848 Pending DE1241834B (de) | 1962-12-04 | 1962-12-04 | Verfahren zur Herstellung von 5-Nitrothiophenderivaten |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT241451B (enrdf_load_stackoverflow) |
| BE (1) | BE640741A (enrdf_load_stackoverflow) |
| CH (1) | CH445519A (enrdf_load_stackoverflow) |
| DE (1) | DE1241834B (enrdf_load_stackoverflow) |
| GB (1) | GB989604A (enrdf_load_stackoverflow) |
| NL (1) | NL301268A (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE613604A (enrdf_load_stackoverflow) * | 1961-02-08 | 1962-08-07 |
-
0
- BE BE640741D patent/BE640741A/xx unknown
- NL NL301268D patent/NL301268A/xx unknown
-
1962
- 1962-12-04 DE DE1962B0069848 patent/DE1241834B/de active Pending
-
1963
- 1963-12-02 CH CH1471463A patent/CH445519A/de unknown
- 1963-12-03 GB GB4766363A patent/GB989604A/en not_active Expired
- 1963-12-03 AT AT966563A patent/AT241451B/de active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE613604A (enrdf_load_stackoverflow) * | 1961-02-08 | 1962-08-07 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB989604A (en) | 1965-04-22 |
| BE640741A (enrdf_load_stackoverflow) | |
| CH445519A (de) | 1967-10-31 |
| AT241451B (de) | 1965-07-26 |
| NL301268A (enrdf_load_stackoverflow) |
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